a) I-L-P-F
Interpretation:
The structure of the PTH derivative product that is obtained by Edman degradation of the peptide I-L-P-F is to be given.
Concept introduction:
Edmund degradation involves treatment of a peptide with phenyl isothiocyanate, followed by reaction with trifluoroacetic acid when an anilinothiazolinone (ATZ) is produced. This ATZ rearranges in the presence of acids to yield N-phenylthiohydantoin.
To give:
The structure of the PTH derivative product that is obtained by Edman degradation of the peptide I-L-P-F.
b) D-T-S-G-A
Interpretation:
The structure of the PTH derivative product that is obtained by Edman degradation of the peptide D-T-S-G-A is to be given.
Concept introduction:
Edmund degradation involves treatment of a peptide with phenyl isothiocyanate, followed by reaction with trifluoroacetic acid when an anilinothiazolinone (ATZ) is produced. This ATZ rearranges in the presence of acids to yield N-phenylthiohydantoin.
To give:
The structure of the PTH derivative product that is obtained by Edman degradation of the peptide D-T-S-G-A.
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Chapter 26 Solutions
Organic Chemistry
- The Arg-Gly-Asp tripeptide (RGD) is a well-known tumour targeting peptidemotif. Explain how you would synthesise H-Arg-Gly-Asp-OH, starting fromthe constituent amino acids? Explain all steps that are necessary and discuss amechanism for one side chain protection and one C terminus protection.arrow_forwardGiven the following peptideSEPIMAPVEYPK(a) Estimate the net charge at pH 7 and at pH 12. Assume the pKa valuesgiven in Table (b) How many peptides would result if this peptide were treated with(1) cyanogen bromide, (2) trypsin, or (3) chymotrypsin?(c) Suggest a method for separating the peptides produced by chymotrypsintreatment.arrow_forwardA nonapeptide released by globulins in the blood in response to a waspsting. Hydrolysis gives the following amino acids: 2 Arg, Gly, 2 Phe, 3 Pro, and Ser.Edman degradation gives phenylthiohydantoin of Arg. Cleavage with carboxypeptidase gives Arg. Partial hydrolysis gives the following di- and tripeptides: Phe-Ser, Pro-GlyPhe, Pro-Pro, Ser-Pro-Phe, Phe-Arg, and Arg-Pro. What is the amino acid sequence of this peptide?arrow_forward
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- The peptide Proline-Serine-Alanine-Phenylalanine-Glutamine is present at pH 7. Draw the peptide and include stereochemistry.arrow_forwardWhat fragments are produced when the peptide shown below is treated with trypsin? Gly-Arg-Val-Phe -Leu-Lys-Met-Trp-Pro-Tyr-Cys-Serarrow_forwardSuggest a reasonable strategy for the synthesis of the dipeptide Leu-Phe, using established protocol for peptide synthesis.arrow_forward